sort of like motorboating, but you instead of placing your face in between the breasts, one just leans back and "blows the wind into a girls sails" aka breasts less awakward and easier to do in public
hey jess, can i motorboat you?
no way! we're in the middle of a bar, but you can sailboat me!
blow away!
by J BOMMBZ January 27, 2010
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(n.) (synonym for sluts)
-referring to sluts in the manner or basis that girls (sluts) are just like sailboats; riding a sailboat is great fun, just as sailboats are great to look at and examine it's special unique features that every boat does not retain(same with hotties when enjoying tits, ass and facial features); but messing with the masts, the angles, wind direction and whatnot gets old quick.

Similar to playing with the same hottie for an overly extended period of time, you get bored and wanna jump off the boat just as why you always anchor the sailboat, jump off and go for a swim. Even though your sailboat(slut) may be very intriguing and fun to play with, you always want to upgrade.
hence the reason why large sailboats will have a jet ski or jet boat on the back, just as we keep hotties on the backburner.

friend A: Bra, that sailboat wanted to wife me up
friend B: Jesus dude, same here man. thats why i had to sail asap
friend C: ya man, thats why you gotta get on the boat, go for a quick sail around, then hit the docks to find a new boat to sail for a few days
Random Guy: F*cking sailboats
Random Guy's friend: oh sluts sluts sluts
Used in a sentence: got some sexy sailboats out here today
sluts gap
by suzy greenberg114 February 1, 2011
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A three-some consisting of two girls and a guy. The guy lays on his back while one girls rides him and the other sits on his face. The two girls face each other holdings hands, creating a triangle or "Sail".

The same thing as Eiffel tower but for 2 girls, 1 guy.
ddannnggggg! Dina and Snooks really know how to go sailboating!!
by Sailboatking August 11, 2011
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The acting of rocking a mans member (aka sailboat) back and forth inside a womans vagina (aka cum-boat), this process is refered to as surfing her seas, after which the man finishes within her, this process is refered to as "unloading cargo"

*all aspects must be followed to be considered sailboating
Friend 1: "Dude, what'd you do last night?"
Friend 2: "Not much, just some sailboating."
Friend 1: "Idiot! Think she'll get pregnant?"
Friend 2: "I dont care, not my bitch."
by Gary Flongtard December 7, 2011
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The art of coercing a monkey to blow his load into you mouth so you can get high off his jizz.
Bill and Jerry like to go sailboating in the jungles of Costa Rica, because they prefer the old fashion way of getting stoned.
by Agent O November 12, 2010
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A person who embraces the sailboat lifestyle. One who acts better than everyone else, by driving European cars or not waving to no one except people who have sailboats.
Because Norbert likes to sail all day and drive his volvo and never wave to people and act rude and snobby he is considered a Sailboater.

Norbert loves to go sailing and think nothing but of himself.

Branson is from Nantucket, it is the land of Sailboaters.

Boston is a safe haven for Sailboaters, but filled with many assholes. Because they sail.
by Kevin Baines March 4, 2006
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A dick trick.

The man's (or she-man's) penis is wrapped underneath the ball sack till the penis is pulled perpendicular to the body. This is the "boat." Note, the balls remain behind the dick. Then, the scrotum is then stretched into a triangle where base is held against the penis. Note, the top requires pinching the scrotum and pulling up hard, which can be enjoyable or painful. This is the sail. When completed, the penis sailboat appears to be cruising at about 3 knots across the pubis. It's very popular and appropriate for most parties.
Hey, this party needs a kick, should I bust out a sailboat?

Cody's balls are so big his sailboat would be hella' fast.

I was surprised how much she liked my sailboat trick, then she let me dock my boat in her lady bay.
by ucla sailor January 3, 2012
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